When Andrew Stein stepped into the CEO role at the Children's Foundation, he inherited a bloated tech stack, misaligned systems, and a looming CRM renewal with a steep price hike. With no in-house tech experts and only 15 staff, Andrew faced a critical decision point: how to make a smart technology pivot without draining his team's energy—or the organization's resources. In this conversation, he breaks down the structured, people-first approach that helped the foundation unify around its needs, realign its tech strategy, and emerge stronger, all without adding headcount.

Ashok and Andrew unpack the process behind the workshop that set this transition in motion—covering everything from navigating vendor lock-in and defining "non-negotiables," to how sticky notes and cross-functional collaboration became unexpected heroes in a major organizational shift. They also get into broader lessons on change management, trust-building, and how to keep morale high when the work gets hard. Whether you lead a lean nonprofit or a team in transition to transformation, there's something here for anyone looking to make complex changes with clarity and alignment.

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Inside the episode...

• How Andrew prepared his team for a major CRM migration without internal tech specialists

• Why they focused on needs alignment before even thinking about vendors

• The sticky note exercise that set the tone for cross-functional collaboration

• What it means to "de-risk" a big decision through structured prioritization

• The importance of clarity and timing in organizational restructuring

• How Andrew rebuilt staff trust after downsizing from 35 to 13

• The concept of "avoiding the big bang" in tech transitions

• Why hiring a tech advocate (not tied to any vendor) made a difference

• Reapplying product thinking and prioritization tools in hiring and org design

• The mindset shift from one-time dream teams to repeatable team-building

Mentioned in this episode

• Remarkable Tablet

• Integral's Product Success Lab

• The Children's Foundation – yourchildrensfoundation.org

• Andrew's LinkedIn - https://www.linkedin.com/in/andrew-stein-91a16847/

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